Aldehyde Ketone 1y5i5m
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ALDEHYDES AND KETONE
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ALDEHYDES AND KETONES In aldehydes, the carbonyl group is linked to either two hydrogen atom or one hydrogen atom and one carbon containing group such as alkyl, aryl or aralkyl group Examples *
In ketones, the carbonyl group is linked to two carbon containing groups which may be same or different alkyl, aryl group. If two R and R’ groups are same, the ketone is called simple or symmetrical ketone and if R and R’ are different, then ketone is known as mixed or an unsymmetrical ketone.
STRUCTURE Carbonyl carbon of both aldehyde and ketones is sp2 – hybridised, One of the three sp2 hybridised orbital get involved in σ- bond formation with half –filled p-orbital of oxygen atom whereas rest of the two are consumed in σ-bond formation with hydrogen and carbon depending on the structure of aldehyde or ketone. Unhybridised p-orbital of carbonyl carbon form π-bond with another half-filled p-orbital of oxygen atom by sideways overlapping.
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ISOMERISM IN ALDEHYDES AND KETONES (a) Chain isomerism: Aldehydes ( with 4 or more carbon atoms) and ketone ( with 5 or more carbon atoms) show chain isomerism. Example i) C4H8O CH3-CH2-CH2-CHO ( butanal)
ii)
C5H10O
(b) Position isomerism: aliphatic aldehydes do not show position isomerism, because –CHO group is always present at the end of carbon chain. Aromatic aldehyde show position isomerism. Example (c) Metamerism: Higher ketones show metamerism due to presence of different alkyl groups attached to the same functional group C5H10O
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(d) Functional isomerism : Aldehydes and ketones show functional isomerism in them. In addition, they are also related to alcohols, ethers and other cyclic compounds. Example C3H6O
(e) Tautomerism : Aldehydes and ketones also show tautomerism (I) C2H4O
(II)
C3H6O
GENERAL METHODS OF PREPARATION OF ALDEHYDES AND KETONES 1. From alcohol (i) Oxidation of alcohol
3
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Since the oxidizing agent used in the above reactions is a strong oxidizing agent, it oxidizes aldehydes and ketone further to carboxylic acids To prevent further oxidation, a mild oxidizing agent such as pyridinium chlorochromate (pcc), CrO3.C5H5N∙HCl or CrO3NH+CrO3Cl- are used Collin’s reagent [ (C5H5N)2 ∙CrO3] can also used.
(ii)
Catalytic dehydrogenation of alcohols
2. From alkenes (i) Reductive ozonolysis of alkenes.
(ii)
Wacker process.
4
ALDEHYDES AND KETONE (iii)
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OXO process [Carbonylation / Hydroformylation]
3. From alkynes
4. From Grignard reagent (1) By addition to ester
5
ALDEHYDES AND KETONE (iii)
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By addition to nitriles
5. From carboxylic acids (i) Catalytic decomposition of carboxylic acid.
(ii)
From calcium salt of carboxylic acids
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ALDEHYDES AND KETONE
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6. From derivatives of carboxylic acids (i) Reduction of acid chlorides ( Rosenmund’s reaction)
Above reaction is known as Rosenmund’s reduction and is applicable for preparation of aldehydes BaSO4, sulphur act as poison for Pd catalyst and prevents reduction of RCHO into RCH2OH (ii) Reduction of acid chloride with dialkyl cium.
Reduction of acid chloride into ester can also be carried out by lithium tri-t-butoxy aluminium hydride, LiAlH[OC(CH3)3]3
(iii)
Reduction of esters
7. From gem-dihalides by hydrolysis
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ALDEHYDES AND KETONE
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8. From nitriles by reduction (i) Stephen’s reduction.
(ii)
Reduction with LiAlH4
9. Preparation of aromatic carbonyl compounds. (i)
This is known as etard reaction (ii) By side chain chlorination followed by hydrolysis
8
ALDEHYDES AND KETONE (iii)
Gatterman – Koch reaction
(iv)
Friedel Craft Acylation
(v)
Reimer – Tiemann reaction
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ALDEHYDES AND KETONE
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PHYSICAL PROPERTIES OF ALDEHYDES AND KETONE
1. Physical state Lower of aldehydes and ketones (upto C10) are colourless volatile liquids except formaldehyde which is gas at ordinary temperature Higher of aldehyde and ketones are solids with fruity odour Lower aldehydes have unplesent odour but ketones posses pleasant smell 2. Boiling point Boiling point of aldehyde and ketones is slightly lower than corresponding alcohol due to lack of hydrogen bonding. However their boiling point is slightly higher than that of corresponding non-polar hydrocarbon or weakly polar ether. This may attributed to reason that aldehydes and ketones are polar compounds and thus possess intermolecular dipoledipole interaction
Among isomeric aldehydes and ketones, boiling point of ketones is slightly higher than that of aldehydes due to the presence of two electron donating alkyl groups making them more polar. 3. Solubility Lower of aldehydes and ketones ( upto C4) are soluble in water due to H-bonding between polar carbonyl group and water. However, solubility decreases with increase in molecular weight Aromatic aldehydes and ketones are much less soluble than corresponding aliphatic aldehydes and ketones due to large benzene ring. However all carbonyl compounds are fairly soluble in organic solvents.
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ALDEHYDES AND KETONE
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RELATIVE REACTIVITY OF ALDEHYDES AND KETONES Aldehydes are more reactive than ketones on of the following facts: (a) Aliphatic aldehydes and ketones (i) Inductive effect: The reactivity of the carbonyl group towards the addition reaction depends upon the magnitude of the positive charge on the carbonyl carbon atom. Hence, any substituent that increases the positive charge on the carbonyl carbon must increase its reactivity towards addition reactions. The introduction of negative group ( -I effect) increases the reactivity, while introduction of alkyl group (+I effect) decreases the reactivity, therefore, greater the number of alkyl groups attached to the carbonyl group and hence, lower is its reactivity towards nucleophilic addition reactions. Thus, the following decreasing order of reactivity is observed
(ii) Steric effect In formaldehyde there is no alkyl group while in all other aldehyde there is one alkyl group so here the nucleophile attack is relatively more easy but in ketones there are two alkyl groups attached to carbonyl group and these causes hinderance, to the attacking group. This factor is called steric hinderance (crowding). In other words the hindrance increases, the reactivity decreases accordingly. Thus order of reactivity is
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(b) Aromatic aldehydes and ketones In general, aromatic aldehydes and ketones are less reactive than the corresponding aliphatic aldehydes and ketones. It is due electron releasing resonance effect of bezene eing
Due to electron releasing resonance effect (+R effect) of benzene ring, the magnitude of positive charge on carbonyl group decreases and consequently it becomes less susceptible to nucleophilic attack.
The order of reactivity of aromatic aldehydes and ketones is
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ALDEHYDES AND KETONE
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CHEMICAL PROPERTIES OF ALDEHYDES AND KETONES Nucleophilic addition reaction
In this reaction carbon atom of carbonyl group changes from sp2 to sp3 hybridised (i) Addition of hydrogen cyanide (HCN)
Mechanism Step I : The hydrogen cyanide interacts with the base to form nucleophile
Step II : The nucleophile attacks the carbonyl carbon to form an anion
StepIII: The proton from the solvent (usually water) combines with the anion to form cyanohydrine.
Cyanohydrins are formed by all aldehydes but in ketones, only acetone, butanone, 3pethenone and pinacolone form cyanohydrins.
13
ALDEHYDES AND KETONE (ii)
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Addition of sodium bisulphate (NaHSO4)
All ketones do not undergo this reaction only methyl ketone form addition product with sodium bisulphate On reacting the crystalline solid bisulphate derivative with dilute HCl or alkali, these adducts decompose to regenerate the original aldehyde or ketones. Hence, this reaction is used in the separation and purification of aldehydes and ketones from non-carbonyl compounds.
(iii)
Addition of Grignard reagent
Formaldehyde form a primary alcohol
14
ALDEHYDES AND KETONE
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Higher aldehydes give secondary alcohol
Ketone give tertiary alcohols
(iv)
Addition of alcohols
Dry HCl protonates the oxygen atom of the carbonyl compounds and therefore, increases the electrophilicity of the carbonyl carbon and hence facilitating the nucleophilic attack by the alcohol molecule. Dry HCl gas also absorbs the water produced in these reactions and thereby shifting equilibrium in forward direction. Ketals can be prepared by treating the ketone with ethyl ortho formate
15
ALDEHYDES AND KETONE
(v)
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Addition of ammonia derivative
Z = OH, NH2 , NHC6H5 , NHCOCH2 etc. The reaction of ammonia derivatives to aldehydes and ketones is called by acids Mechanism Step I: In acidic medium, the carbonyl oxygen gets protonated.
Step II : In ammonia derivatives, the nitrogen atom has a lone pair of electrons, which attack the positively charged carbonyl carbon and results in positive charge on nitrogen atom
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ALDEHYDES AND KETONE
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Step III : The unstable intermediate loses a proton, H+ and water molecule to form stable product (imines)
(vi)
Addition of alkynes
This reaction is also known as ethinylation 2. Reduction reactions I.
Catalytic reduction to alcohol
II.
Clemmensen reduction
17
ALDEHYDES AND KETONE III.
Wolf-Kishner reduction
IV.
Reduction with HI + P (red)
V.
Reduction to pinacols
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3. Oxidation reactions i.
Oxidation with mild oxidizing agents
Ketones are not oxidized by mild oxidizing agents (a) Aldehydes reduces Tollen’s reagent to metallic silver which appears as a silver mirror on wall of test tube. Thus the reaction is also known as silver mirror test.
18
ALDEHYDES AND KETONE
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(b) Reduction of Fehling’s solution Fehling’s solution is an alkaline solution of CuSO4 mixed with Rochelle slat i.e. sodium potassium tartarate. Aldehydes reduces cupric ion (Cu2+) of Fehling’s solution to cuprous ions (Cu+) to form red precipitate of cuprous oxide
ii.
Fehling’s solution is reduced by aliphatic aldehydes only. Aromatic aldehydes and ketones so not give this reaction. Oxidation with strong oxidizing agent
iii.
Haloform reaction
4. Condensation reactions (1) Aldol condensation
19
ALDEHYDES AND KETONE
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Mechanism
Aldehyde or ketones which do not contain α-hydrogen atom like formaldehyde (HCHO), benzaldehyde (C6H5CHO) and benzophenone (C6H5COC6H5) do not undergo aldol condensation.
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ALDEHYDES AND KETONE
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(2) Cross aldol condensation
# A- A Condensation
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ALDEHYDES AND KETONE
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# B-B Condensation
# A-B Condensation
# B-A Condensation
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ALDEHYDES AND KETONE
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(3) Claisen – Schmidt condensation
5. Cannizzaro reaction
Mechanism Step I : The OH- ion attacks the carbonyl carbon to form hydroxyl alkoxide
Step II : Anion (I) acts as hybride ion donor to the second molecule of aldehyde. In the final step of the reaction, the acid and the alkoxide ion transfer H+ to acquire stability.
23
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6. Reaction with chloroform
Chloretone is used as hypnotic. 7. Reaction with primary amine
8. Electrophilic substitution reaction of aromatic carbonyl compounds
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ALDEHYDES AND KETONE
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USES OF ALDEHYDES AND KETONES (a) Uses of formaldehyde i. The 40% solution of formaldehyde in water ( formaline) is used as disinfectant, germicide and antiseptic. It is used for the preservation of biological specimens ii. It is used for silvering of mirrors iii. It is used for making synthetic plastics, like Bakelite, urea- formaldehyde resin etc (b) Uses of acetaldehyde i. It is used in preparation of acetic acid, dyes, drugs, etc ii. As an antiseptic inhalant in nose troubles (c) Uses of benzaldehyde i. As flavouring agent in perfume industry ii. In manufacture of dyes. (d) Uses of acetone i. As a solvent for cellulose acetate, resin etc. ii. As a nailpolish remover iii. In the preparation of an artificial scent and synthetic rubber
25
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ALDEHYDES AND KETONES In aldehydes, the carbonyl group is linked to either two hydrogen atom or one hydrogen atom and one carbon containing group such as alkyl, aryl or aralkyl group Examples *
In ketones, the carbonyl group is linked to two carbon containing groups which may be same or different alkyl, aryl group. If two R and R’ groups are same, the ketone is called simple or symmetrical ketone and if R and R’ are different, then ketone is known as mixed or an unsymmetrical ketone.
STRUCTURE Carbonyl carbon of both aldehyde and ketones is sp2 – hybridised, One of the three sp2 hybridised orbital get involved in σ- bond formation with half –filled p-orbital of oxygen atom whereas rest of the two are consumed in σ-bond formation with hydrogen and carbon depending on the structure of aldehyde or ketone. Unhybridised p-orbital of carbonyl carbon form π-bond with another half-filled p-orbital of oxygen atom by sideways overlapping.
1
ALDEHYDES AND KETONE
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ISOMERISM IN ALDEHYDES AND KETONES (a) Chain isomerism: Aldehydes ( with 4 or more carbon atoms) and ketone ( with 5 or more carbon atoms) show chain isomerism. Example i) C4H8O CH3-CH2-CH2-CHO ( butanal)
ii)
C5H10O
(b) Position isomerism: aliphatic aldehydes do not show position isomerism, because –CHO group is always present at the end of carbon chain. Aromatic aldehyde show position isomerism. Example (c) Metamerism: Higher ketones show metamerism due to presence of different alkyl groups attached to the same functional group C5H10O
2
ALDEHYDES AND KETONE
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(d) Functional isomerism : Aldehydes and ketones show functional isomerism in them. In addition, they are also related to alcohols, ethers and other cyclic compounds. Example C3H6O
(e) Tautomerism : Aldehydes and ketones also show tautomerism (I) C2H4O
(II)
C3H6O
GENERAL METHODS OF PREPARATION OF ALDEHYDES AND KETONES 1. From alcohol (i) Oxidation of alcohol
3
ALDEHYDES AND KETONE
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Since the oxidizing agent used in the above reactions is a strong oxidizing agent, it oxidizes aldehydes and ketone further to carboxylic acids To prevent further oxidation, a mild oxidizing agent such as pyridinium chlorochromate (pcc), CrO3.C5H5N∙HCl or CrO3NH+CrO3Cl- are used Collin’s reagent [ (C5H5N)2 ∙CrO3] can also used.
(ii)
Catalytic dehydrogenation of alcohols
2. From alkenes (i) Reductive ozonolysis of alkenes.
(ii)
Wacker process.
4
ALDEHYDES AND KETONE (iii)
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OXO process [Carbonylation / Hydroformylation]
3. From alkynes
4. From Grignard reagent (1) By addition to ester
5
ALDEHYDES AND KETONE (iii)
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By addition to nitriles
5. From carboxylic acids (i) Catalytic decomposition of carboxylic acid.
(ii)
From calcium salt of carboxylic acids
6
ALDEHYDES AND KETONE
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6. From derivatives of carboxylic acids (i) Reduction of acid chlorides ( Rosenmund’s reaction)
Above reaction is known as Rosenmund’s reduction and is applicable for preparation of aldehydes BaSO4, sulphur act as poison for Pd catalyst and prevents reduction of RCHO into RCH2OH (ii) Reduction of acid chloride with dialkyl cium.
Reduction of acid chloride into ester can also be carried out by lithium tri-t-butoxy aluminium hydride, LiAlH[OC(CH3)3]3
(iii)
Reduction of esters
7. From gem-dihalides by hydrolysis
7
ALDEHYDES AND KETONE
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8. From nitriles by reduction (i) Stephen’s reduction.
(ii)
Reduction with LiAlH4
9. Preparation of aromatic carbonyl compounds. (i)
This is known as etard reaction (ii) By side chain chlorination followed by hydrolysis
8
ALDEHYDES AND KETONE (iii)
Gatterman – Koch reaction
(iv)
Friedel Craft Acylation
(v)
Reimer – Tiemann reaction
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9
ALDEHYDES AND KETONE
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PHYSICAL PROPERTIES OF ALDEHYDES AND KETONE
1. Physical state Lower of aldehydes and ketones (upto C10) are colourless volatile liquids except formaldehyde which is gas at ordinary temperature Higher of aldehyde and ketones are solids with fruity odour Lower aldehydes have unplesent odour but ketones posses pleasant smell 2. Boiling point Boiling point of aldehyde and ketones is slightly lower than corresponding alcohol due to lack of hydrogen bonding. However their boiling point is slightly higher than that of corresponding non-polar hydrocarbon or weakly polar ether. This may attributed to reason that aldehydes and ketones are polar compounds and thus possess intermolecular dipoledipole interaction
Among isomeric aldehydes and ketones, boiling point of ketones is slightly higher than that of aldehydes due to the presence of two electron donating alkyl groups making them more polar. 3. Solubility Lower of aldehydes and ketones ( upto C4) are soluble in water due to H-bonding between polar carbonyl group and water. However, solubility decreases with increase in molecular weight Aromatic aldehydes and ketones are much less soluble than corresponding aliphatic aldehydes and ketones due to large benzene ring. However all carbonyl compounds are fairly soluble in organic solvents.
10
ALDEHYDES AND KETONE
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RELATIVE REACTIVITY OF ALDEHYDES AND KETONES Aldehydes are more reactive than ketones on of the following facts: (a) Aliphatic aldehydes and ketones (i) Inductive effect: The reactivity of the carbonyl group towards the addition reaction depends upon the magnitude of the positive charge on the carbonyl carbon atom. Hence, any substituent that increases the positive charge on the carbonyl carbon must increase its reactivity towards addition reactions. The introduction of negative group ( -I effect) increases the reactivity, while introduction of alkyl group (+I effect) decreases the reactivity, therefore, greater the number of alkyl groups attached to the carbonyl group and hence, lower is its reactivity towards nucleophilic addition reactions. Thus, the following decreasing order of reactivity is observed
(ii) Steric effect In formaldehyde there is no alkyl group while in all other aldehyde there is one alkyl group so here the nucleophile attack is relatively more easy but in ketones there are two alkyl groups attached to carbonyl group and these causes hinderance, to the attacking group. This factor is called steric hinderance (crowding). In other words the hindrance increases, the reactivity decreases accordingly. Thus order of reactivity is
11
ALDEHYDES AND KETONE
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(b) Aromatic aldehydes and ketones In general, aromatic aldehydes and ketones are less reactive than the corresponding aliphatic aldehydes and ketones. It is due electron releasing resonance effect of bezene eing
Due to electron releasing resonance effect (+R effect) of benzene ring, the magnitude of positive charge on carbonyl group decreases and consequently it becomes less susceptible to nucleophilic attack.
The order of reactivity of aromatic aldehydes and ketones is
12
ALDEHYDES AND KETONE
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CHEMICAL PROPERTIES OF ALDEHYDES AND KETONES Nucleophilic addition reaction
In this reaction carbon atom of carbonyl group changes from sp2 to sp3 hybridised (i) Addition of hydrogen cyanide (HCN)
Mechanism Step I : The hydrogen cyanide interacts with the base to form nucleophile
Step II : The nucleophile attacks the carbonyl carbon to form an anion
StepIII: The proton from the solvent (usually water) combines with the anion to form cyanohydrine.
Cyanohydrins are formed by all aldehydes but in ketones, only acetone, butanone, 3pethenone and pinacolone form cyanohydrins.
13
ALDEHYDES AND KETONE (ii)
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Addition of sodium bisulphate (NaHSO4)
All ketones do not undergo this reaction only methyl ketone form addition product with sodium bisulphate On reacting the crystalline solid bisulphate derivative with dilute HCl or alkali, these adducts decompose to regenerate the original aldehyde or ketones. Hence, this reaction is used in the separation and purification of aldehydes and ketones from non-carbonyl compounds.
(iii)
Addition of Grignard reagent
Formaldehyde form a primary alcohol
14
ALDEHYDES AND KETONE
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Higher aldehydes give secondary alcohol
Ketone give tertiary alcohols
(iv)
Addition of alcohols
Dry HCl protonates the oxygen atom of the carbonyl compounds and therefore, increases the electrophilicity of the carbonyl carbon and hence facilitating the nucleophilic attack by the alcohol molecule. Dry HCl gas also absorbs the water produced in these reactions and thereby shifting equilibrium in forward direction. Ketals can be prepared by treating the ketone with ethyl ortho formate
15
ALDEHYDES AND KETONE
(v)
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Addition of ammonia derivative
Z = OH, NH2 , NHC6H5 , NHCOCH2 etc. The reaction of ammonia derivatives to aldehydes and ketones is called by acids Mechanism Step I: In acidic medium, the carbonyl oxygen gets protonated.
Step II : In ammonia derivatives, the nitrogen atom has a lone pair of electrons, which attack the positively charged carbonyl carbon and results in positive charge on nitrogen atom
16
ALDEHYDES AND KETONE
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Step III : The unstable intermediate loses a proton, H+ and water molecule to form stable product (imines)
(vi)
Addition of alkynes
This reaction is also known as ethinylation 2. Reduction reactions I.
Catalytic reduction to alcohol
II.
Clemmensen reduction
17
ALDEHYDES AND KETONE III.
Wolf-Kishner reduction
IV.
Reduction with HI + P (red)
V.
Reduction to pinacols
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3. Oxidation reactions i.
Oxidation with mild oxidizing agents
Ketones are not oxidized by mild oxidizing agents (a) Aldehydes reduces Tollen’s reagent to metallic silver which appears as a silver mirror on wall of test tube. Thus the reaction is also known as silver mirror test.
18
ALDEHYDES AND KETONE
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(b) Reduction of Fehling’s solution Fehling’s solution is an alkaline solution of CuSO4 mixed with Rochelle slat i.e. sodium potassium tartarate. Aldehydes reduces cupric ion (Cu2+) of Fehling’s solution to cuprous ions (Cu+) to form red precipitate of cuprous oxide
ii.
Fehling’s solution is reduced by aliphatic aldehydes only. Aromatic aldehydes and ketones so not give this reaction. Oxidation with strong oxidizing agent
iii.
Haloform reaction
4. Condensation reactions (1) Aldol condensation
19
ALDEHYDES AND KETONE
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Mechanism
Aldehyde or ketones which do not contain α-hydrogen atom like formaldehyde (HCHO), benzaldehyde (C6H5CHO) and benzophenone (C6H5COC6H5) do not undergo aldol condensation.
20
ALDEHYDES AND KETONE
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(2) Cross aldol condensation
# A- A Condensation
21
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# B-B Condensation
# A-B Condensation
# B-A Condensation
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ALDEHYDES AND KETONE
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(3) Claisen – Schmidt condensation
5. Cannizzaro reaction
Mechanism Step I : The OH- ion attacks the carbonyl carbon to form hydroxyl alkoxide
Step II : Anion (I) acts as hybride ion donor to the second molecule of aldehyde. In the final step of the reaction, the acid and the alkoxide ion transfer H+ to acquire stability.
23
ALDEHYDES AND KETONE
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6. Reaction with chloroform
Chloretone is used as hypnotic. 7. Reaction with primary amine
8. Electrophilic substitution reaction of aromatic carbonyl compounds
24
ALDEHYDES AND KETONE
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USES OF ALDEHYDES AND KETONES (a) Uses of formaldehyde i. The 40% solution of formaldehyde in water ( formaline) is used as disinfectant, germicide and antiseptic. It is used for the preservation of biological specimens ii. It is used for silvering of mirrors iii. It is used for making synthetic plastics, like Bakelite, urea- formaldehyde resin etc (b) Uses of acetaldehyde i. It is used in preparation of acetic acid, dyes, drugs, etc ii. As an antiseptic inhalant in nose troubles (c) Uses of benzaldehyde i. As flavouring agent in perfume industry ii. In manufacture of dyes. (d) Uses of acetone i. As a solvent for cellulose acetate, resin etc. ii. As a nailpolish remover iii. In the preparation of an artificial scent and synthetic rubber
25
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